High Stakes

Welcome back to 2026 with fresh strategic insights.

Singular Focus (Except When It’s Not)

This summer my city did something audacious: it launched two massive pieces of infrastructure within weeks of each other.

The Metro Rail Tunnel: five underground stations, nine kilometres of twin tunnels, $13 billion. The West Gate Tunnel: $10 billion of tolled roadway slicing under industrial heartland and a river. Combined, that’s $23 billion worth of “we’re not turning back now.”

I used both in the week they launched, and I was genuinely impressed. Not just by the engineering — though watching a train glide into a station 30 meters underground is objectively cool — but by what they reveal about strategic bets.

Both were conceived decades ago (Metro in 2005, West Gate in 2015), and both are textbook Big Bets: irreversible Type 2 decisions seeking VLTBMS (Very Long Term Benefit to Multiple Stakeholders). But here’s what struck me as I drove through one tunnel and rode trains through the other: neither works alone.

The Metro connects to existing lines, feeds future airport rail, enables the Suburban Rail Loop. The West Gate only makes sense because the CityLink tollroad already exists, because the Port desperately needs freight access, because the freeway was widened simultaneously. Both will feel “normal” within months, but they’ve already become infrastructure that other mega-projects depend on to succeed.

In my consulting work, I want to see my clients treat their big bets unlike solo performances. Infrastructure — whether it’s a tunnel or a transformation program —never performs alone. Your diversity initiative needs your recruitment system redesigned. Your digital strategy needs your governance model updated. Your innovation lab needs your risk framework loosened.

Everything connects.

Question: What is the SINGLE biggest investment (of money, effort, time) that you will make this year? And what does it enable?

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Grand Slam

I’m a tennis tragic, and the Australian Open has just started. Today, 128 men and 128 women are in the draw. In two weeks, only two of them — one of each — will lift a trophy. Everyone else goes home having lost their last match.

I love this about Grand Slams. It’s ruthlessly binary. You’re either good enough on the day, or you’re not. There’s no “pretty good” trophy. Lose one match and you’re on a plane home. The format demands peak performance when it matters, not when it’s convenient.

Now, here’s the thing. Most strategy work isn’t like this at all. Usually good strategy involves portfolio thinking: spread risk, test and learn, fail fast. That’s smart. But here’s how to tell the difference: Can you recover from failure? If a pilot program flops, can you redesign and try again? That’s portfolio. If the major donor decision happens once, the regulatory window closes, or the merger collapses, that’s Grand Slam. You get one shot.

In my work, I see both logic errors: teams treating irreversible moments like experiments (under-preparing for the binary), and treating experiments like Grand Slams (over-preparing for what should be iterative learning).

Question: What's one high-stakes decision coming up where you need clarity on whether it's portfolio or Grand Slam—and are you resourcing it accordingly?

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When Boards Override Expertise

If you’re a reader, and Australian, you’ve no doubt followed the implosion of the Adelaide Writers’ Week.

The board cancelled a Palestinian Australian author citing “cultural sensitivity” after the Bondi terror attack, triggering 180+ speaker withdrawals, the resignation of the entire board and director Louise Adler, and ultimately the festival’s cancellation.

It won’t surprise you to know I’ve followed this as a governance failure (admittedly with morbid fascination). Here we had a highly respected board and CEO. A landmark, nationally significant event. Popular with punters. The publishing industry depends upon it.

Then: total meltdown within five days.

What went wrong? The board overrode their expert curator on a programming decision. They had no artists or writers among them. When backlash hit, they had limited legitimacy to stand on. And nowhere to back down to.

In my work with boards governing public value organisations (think research institutes, health services, infrastructure agencies, educational organisations) I see directors who are content experts sitting alongside experts in finance, law, marketing, government relations. The trap is thinking board expertise in one domain gives you decision rights in another. Decision rights need to be explicit: Who decides programming? Who decides budget? Who decides ethical parameters? Where does the board govern, and where does expert leadership lead?

Question: Does your board have decision rights that protect both governance oversight and operational expertise?

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I hope your year has started with the same energy mine has: full of prospects, opportunity, and strategic challenges worth solving.

If you're thinking about your big bets for 2026 and want a sounding board, reach out to me at ah@workwell.com.au. I've got capacity for new work and I'd genuinely enjoy the conversation.

As always, click the heart if today's 5MSM resonated, and I'll see you here next week.

Andrew